PILOTing A New Career Direction Transcript

More Elephant Intro

Jason Rudman: Welcome to what is the first More Elephant podcast. I am so excited to be in conversation over the next. A few weeks, months, years, it might seem, around topics that I think are really important that we're having conversations about.

Thought leadership for today's world. And as I thought about the first series of conversations that I wanted to have, I have come back to post-pandemic, this changing nature of the thing that we call work. One of the things that I'm doing is eaching out on a five-year-plus dream and launching a thought leadership platform that's a blog, a podcast. I'm in the throes of writing a book and I see a real journey ahead of me in terms of this construct of post-pandemic saying less and listening more to each other so that we can individually and collectively ideate and create change. That ultimately helps us listen, learn, and live better.

And what better way to start than my first guest, Ben Brooks, who is a friend, but is also an entrepreneur, incredibly dynamic, a seasoned executive HR professional has been on this journey, this More Elephant journey. For the last five years in the capacity of being my executive coach. So, he's probably going to spill some knowledge and as well as fill some secrets about the More Elephant journey as we get into this conversation.

But as I thought about the changing nature of work, what I'm struck by is the company that Ben has built Pilot that is all about. The people that they serve “feeling powerful at work.” So, in the connection with More Elephant and listening to what's around us and learning from some of the best in the business, I want to welcome Ben Brooks to the first More Elephant podcast.

[00:02:29] Ben Brooks: What an honor to be here, Jason. And I know that this has been a journey to get here. Anyone that doesn't create never has the sense of just how hard it is to do anything new from scratch. So, I'm really glad to be christening this amazing thought leadership platform with you in and being in a conversation and learning from you as well.

[00:02:45] Jason Rudman: Well, Ben, thanks, and what a way to jump in.

For those of you listening, we are not that scripted. We've got a narrative that we think we're going to follow, but you just talked about the creative process and how hard it is.

So, for those listeners who are like, Ben Brooks. Who is this guy? What does he do? Where has he been? Would you take people on a journey as to who you are and what your power alley is? And then we're going to get into some More Elephant moments there because within your journey, I know there was the corporate train, and then the corporate train stopped. And he became an entrepreneur. But if you take us back, who is Ben Brooks? And how did he get to this place in time?

[00:03:30] Ben Brooks: You know, my career has been V-shaped, meaning I've done a lot of different things that when I look backwards, they connect and they make sense. But it was never a forward-looking plan to say, Oh, I'm going to do this, this, this, and this.

And I remember Steve Jobs only gave one commencement address ever, and it was at Stanford, and I watched it on YouTube. And he talked about, you can connect the dots in your career backwards. And it really clicked for me in that regard.

And, you know, a lot of my career in life has been around experimentation, luck, adversity, curiosity, adventure. Where I'm at now and what I feel in my purpose is really helping people, you know, feel powerful at work and powerfully command their lives.

People say “large and in charge,” really from the inside out, and there's just so much of work, but also our lives, that we can affect, right? That we can design around what matters to each of us. And oftentimes, there's a lot of learned helplessness, things where we condition ourselves.; there's not much to do or some cynicism or passivity in action, which gets in my craw, and so I really try to help people get more of what they want.

Fundamentally, coaching is about helping clients get what they want, which sometimes means defining what that is. And then often navigating the, you know, not so linear path of getting it and making it and creating it.

So, what I wanted to do for myself if I had to coach myself was to have impact at scale. I did an executive coaching offsite about a decade ago and we had to say, what is the KPI for our life? And for me, it was impact. It wasn't about fame or wasn't about wealth or wasn't about just having to boondoggle all the time.

I want to know that. If I have a, you know, a gravestone, (I want to be cremated), but if I have a gravestone, it, you know, says made a big impact, used up. And so that's what I'm on the journey of building right now with my company, and what I do, is this idea that has people have more of what they want for them to feel powerful and for them to have the impact that they want in their lives.

[00:05:29] Jason Rudman: I love the word impact again. For our listeners, we've known each other for a number of years. We've been on a very interlocked journey through coaching and friendship and brotherhood over the last five years. And I think that well I know the word impact not only resonates with you but resonates with me. It's not about the fame. It's ultimately for me about what I can do to change other people's lives for the better.

And again, I think the dots that you talked about having the benefit and the wisdom to be able to go back into your history and say, ah, I may not have known what that moment was right there, but that moment connects to all of these other moments and gets me here is again synonymous what More Elephant is about, which is about ideation and talking to change agents that are rethinking how we think about these big constructs and making sometimes small changes along the way to enable us to live better.

I want to jump right in. And, there's a little bit of a narrative right there. I know enough to say about you that says corporate train, HR executive, incredibly successful.

And then like many of us, there's a moment or a series of moments – I call them More Elephant moments, I really do - where we're not so much communicating out, but we're listening in to what's important to us, the values that we hold dear, the impact that we want to have.

And then you wake up one morning and say, this is the day where that's no longer where I need to be. I need to be charting an entrepreneurial journey that is Pilot. Can you talk to us through that period in your life, what that was like, and what you actually had to go through in order to birth the company?

[00:07:18] Ben Brooks: Yeah, it was birthed from kind of a moment of reset or failure or awareness, you know.

I had always thought of myself as a suit if you will. You know, dressing up in proper business attire, shirt and tie. it was getting a title, becoming a Vice President, it was, you know, having an office, it was making money, having status, you know, having a team, and very sort of traditional status accoutrements of power. And I started to do that. And I not just was a Vice President, I was a Senior Vice President, and I had very nice suits and ties. I had a team across four continents, and I was making very good money, especially for my age and relative to my peers. And while I was succeeding at doing that, the other S word, satisfaction, wasn't always there.

And part of it, you know, being gay, a survival strategy for me has always been having my independence, right? That I will be successful to kind of makeup for maybe, you know, feeling a little bit delayed in life or ostracized or these other things as a way to kind of, to counterbalance or mitigate some of those things.

And so I did that really well, right? I survived and I had the success to do that, but I got to a place in my corporate career, which could have gone in a lot of different directions in the corporate world, and I didn't ever realize or really want to be an entrepreneur.

In fact, being an entrepreneur is a bit of a nightmare. I don't recommend it for most people. I think we fetishize it in the media and we, it sounds great. And everyone's to be their own boss and things. But before you go quit your job and start a business, listening to a podcast like this, take a beat. There's lots of ways to be intrapreneurial or to scratch an entrepreneurial spirit without completely abandoning a job or an income, which I think is, is pretty, you know, important.

[00:09:04] Jason Rudman: I put my hand up on that. That's one thing we learned; I learned through you, which is how far do you want to push that entrepreneurial spirit.

[00:09:11] Ben Brooks: Yeah. And, and I think for me, I had seen, you know, my grandfather was an immigrant and was an entrepreneur. You know, my brother-in-law, I've had other family members and friends do it. And I always thought, oh, that's stressful. That seems tough. I can't imagine doing that.

So it wasn't that I always pined or dreamed of setting up my own shop or doing that. It was more that I had realized that the higher up I went in my organization and the larger the organizations that I worked at, paradoxically, the harder it was to have impact.

You know, organizations by a function of their own survival, the larger the end, the number of people, the number of offices, the amount of revenue, it's at the footprint, the harder it is for a single person to impact them because although it seems great to impact in a positive, you also could impact in a negative. And so, for their own survival, there's a certain stasis built into them, and I realized, that wasn't really the right platform for me.

And entrepreneurship really found me because people, you know, like you, started reaching out and saying, “Hey, let's work in a coaching capacity”. I started doing that on an individual basis, but it wasn't really until a friend of mine, Brian Kelly, who is an entrepreneur (he founded The Points Guy), and we were in the front seat of his car once, and he's like, well, what's the “Points Guy” of careers? What's the thing that helps you help more people do that?

Because Brian started “The Points Guy” doing one-to-one concierge service. Helping you take your membership rewards points and redeem them for a super great flight on ANA to Japan or something like that. But he realized, he's like, I can't help enough people in a one-to-one model.

And it was the same sort of thing with careers, in that I certainly believe in one-to-one executive coaching, but it typically only gets to about 1 percent of salaried employees yet it's very effective. And I thought, what do we do to for a fraction of the cost, deliver almost the same value, you know, at scale to have impact, right?

It was less of a business model question, but really an impact question. And so that's really where I said, let me take, I gave myself some time and some money to experiment in doing that. And that was, you know, it was 10 years ago that I had left the corporate world this last winter. And I've been working on the Pilot journey for nearly nine years, I guess, actually, believe it or not, I'm looking at the data now, it was last week that it was nine years ago that I started my first meeting and paid my first consultant was last week. So that's been a part of the journey along the way. And again, one that I'm still to this day surprised that I'm on because it found me a higher power was definitely at play.

[00:11:40] Jason Rudman: So much to unpack. The first thing, if I were a better friend, I would know what the ninth-anniversary gift is, and it would be at your table right now. I don't think it's wood. So, I think I'm good. I don't think it's wood. I don't think it's paper, but we'll figure out nine. So, congratulations on nine (9) years of Pilot.

And I think for everybody, they should understand you were all in. I mean, this is life savings, life work. This was, you were not, “Oh, one foot in one foot out,” and I think to your point, entrepreneurship is not for everyone. It found you. I think it found a good home. It's not been without its trials and tribulations.

So you go from like one to 10; I can fit ten (10) people in my coaching model to essentially democratize coaching, within any organization of any size. So what's the Pilot framework?

I think what we're going to hear from you about is that self-direction is really important. But I know that Pilot is so much more than “Well, I'm going to teach you how to be self-directed.”

So how should people think about Pilot in the context of the changing nature of work and the changing nature of what it means to manage talent?

[00:12:50] Ben Brooks: It's a great question and I'll probably come back to one of the things I've realized about entrepreneurship as a place to start is…a lot of people think you have to have a great idea. Everyone's like, I don't have the idea, what's the idea, what's the idea?

Almost always the ideas don't work out. And you hear the stories of all the pivots, and all the evolutions, and all the lucky moments. What typically I think great entrepreneurs or really great product-centric entrepreneurs do, and what I've found has worked at Pilot, is you fall in love with the problem, not your solution to the problem.

The problem I was falling in love with was the fact that people were miserable at work and not managing their careers well, right? I've fallen in love with that problem. And that's a problem I learned to kind of have an R&D feel with the one-to-one coaching. What works? What doesn't work about that?

But what I started to look at is when we built Pilot out that we couldn't just duplicate the one-to-one. We had to from a design-thinking perspective, kind of re-imagine what people needed. Because when I work with someone at your tier or your level, you have gotten a lot of feedback. You've been through 360s. You've had a lot of reviews. People that are earlier and emerging in careers often don't know, don't have the feedback, they don't know what they need to work on.

So rather than a super bespoke approach, we took a shared development plan. What's the 80, 20, what most employees need to work on developmentally if they're part of the 99 percent of salaried employees who've never had coaching or formal mentoring? That was a big part of it, which is distinct from, you know, the one-to-one, very highly bespoke process.

We also realized that, you know, people that are earlier in career have less control over their calendars and they can be distracted when there's a lot of pressure on their time, whereas an executive can have an assistant say, “Hey, block off this time and you can go meet with your coach, Ben.” So we used a cohort or a group model where people learn together, which have stickier outcomes. Anytime people do things together, generally, you know, train for a race, save money, lose weight, get sober, they have better outcomes.

We did a deep, cohort-based learning model. So shared development plan, cohort-based learning model. The third thing is we made it virtual - people thought we were NUTS. Everyone thought, “Oh, this has got to be in person, you got to do it in the ballroom of Sheraton or at the headquarters.” But, you know, back in 2014, when we started all this, I thought, I think the future of this is it being where people want, wherever they are.

And it's before remote and hybrid was popular, but that was a big part of the virtual, so it could meet employees that were in different geographies or in the field, etc. Then over time, we realized that it also had to collect a lot of data and be easy for HR to implement.

And also involve other people at an organization, because too often, therapy or coaching could be similar, in that you have a person you say, I'm going to go provide you a coach and they go off to talk to a stranger outside of the context for a very private, opaque conversation, which can be really beneficial, but the rest of the environment doesn't have any idea what's going on.

So, we brought in the managers and the executives and HR, not only in the cohort model but also as additional stakeholders to make it about really shaping the ecosystem and the unit of change of the individual.

So, kind of put all of that together - what's in a six-month virtual program that's affordable, that companies can afford to invest in people early in career – and that's where Pilot is today. And we've won HR product of the year and a bunch of DEI and innovation awards. Nine (9) years into the journey, we're still in love with the same problem. But the solution we started with, which is a totally different thing that we marketed differently and priced differently, it's radically evolved over time, and it's all been from learning.

[00:16:16] Jason Rudman: It's classic design-thinking to your point; that's design-thinking on steroids. And what I appreciate about the model is you're not divorcing the person from the professional setting that they're in and there's an involvement of the team such that, because in my experience, and you've been on the other side, the sheet of paper comes out, the three columns come out, we're going to do three development areas and we're going to invariably put it in the sock drawer, because what we do is the way then say, oh, we're going to have a development conversation every three to six months and in those three months, not a lot of feedback happens.

Or feed forward. I heard the whole conversation about feed forward. I was listening to NPR the other day about, you know, we should be calling it feed-forward and not feedback. We should be looking forward…maybe a conversation for another time, I don't know. Again, I think it's the intersection, of course, you know, embedded in your solution, that it's also technology-enabled. It's a software-enabled experience.

And it gets at the heart of what I think is also important around, and you know, go with me here or clean me up, teaching, and I think a difference between an executive and somebody that's just starting out, but I feel within those six months, you're also heightening awareness such that the user of Pilot can advocate, they understand what agency is. And as I said before, this is a self-directed experience, it’s not, you know, there's no such thing as development in a can where you basically just rip it open and say okay, follow these three things. And then you're going to be fully enabled and your career is going to take off into the stratosphere.

So, I think the agency and the advocacy piece here is really important to the solution you have.

[00:18:01] Ben Brooks: We call that, we said users, we call them members. You know, there's two industries that call their customers users – IT and drug dealers.

So, we try to have them be the, the members, and those members get support from us, right? They need that consistent follow-up. But really the outcomes we're trying to develop are

- How do people solicit feedback so they're more situationally and relationally aware?
- How do they reflect more and tap into the world's leading database of expertise on the individual, which is ourselves? It's our heart and our brains.
- How do they learn to advocate for themselves to speak up about what they want or they need, including to themselves? And
- How do they prioritize their own development as well as invest in relationships?

The ultimate, you know, retention hedge in an organization is a best friend at work. Gallup did all the research in the Vital Friends study. And, and so we're really focused on those things.

And, you know, when you think about from a diversity and inclusion perspective, all this sounds great but the ability to advocate for yourself may be informed by the family you were grown up in, the culture, the creed, the country that you may have been born into.

Some people are born into cultures or environments where they don't have a parent that's in a, maybe a salaried environment. They don't have a role model or coaching or a sibling like that or, or they're raised in a culture where you need to put your head down and you do good work and eventually, be recognized.

Well that doesn't always work and people can't read minds and from diverse perspectives, we often want or need different things than the default setting in a talent system or in an organization or what a manager wants.

And so these are really important skills to harvest, or to harness, I should say, and is what we find is people, while they're powerful at work, they're often powerful in other areas of their life. They learn to advocate in their marriage. They learn to solicit feedback in their community groups. They learn to prioritize themselves with their physical or mental well-being, and these things beyond the core of their job or their profession.

And that's really kind of the vision. While our mission is for everyone to feel powerful at work, the vision of this company is to powerfully command their lives. To be large and in charge around the things that matter to them, which is going to be different based on any single member we have in our program. Everyone's going to have a different configuration of what satisfaction and success look like. We want them to lean into that and get more of what they want, which is what coaching is all about.

[00:20:20] Jason Rudman: I want to get my quadrant view out. You're going to smile. The quadrant view of what's important and to your point, what the plan is for your life, of which I think we're wrestling with in this context of the changing nature of work. That for so often, I am one of those people, my identity was wrapped around what I did, not necessarily who I was.

I can't help but smile as well. I was talking Alvin, my husband for those of you that don't know Alvin, and Alvin and I were on a podcast. We recorded a podcast, and I was asked the question, Ben, who is your role model? And I was a little stumped. So, the traditional answer, of course, my parents.

But as you said, I come from an experience where I'm a first-generation college graduate. So, my role models in terms of how you operate in a professional setting, I didn't really have any that I could point to. And it took me a very long while to build that. And so again, the purpose of Pilot, to not only democratize talent development and to put people on a firm footing, give them the tools to self-direct, but also increase that agency and advocacy of themselves. We've worked together for five years; that does not come overnight. That takes work.

[00:21:37] Ben Brooks: It does. And I think people often only advocate for things they're sure they're going to get, or when they're in a position to have all this leverage against. And, and you don't realize that, you know, the good batting average may be, you know, one-third.

And so we're trying, you know, one of the questions we ask in Pilot is, when's the last time you were told no? It's a good test if you're kind of pushing the limits of advocacy because if you're always hearing yes, you're probably not advocating enough.

And, you know, you mentioned feed forward. I haven't heard it said quite like that, but oftentimes, you know, we have these in-year performance reviews or sometimes they're more frequent. And it's evaluative feedback – did you do this well last year? And we talk about that at Pilot with the managers, that that's essentially looking in the rearview mirror and that's the feedback, and that we talk about the windshield, which is, you know, future-focused feedback that we build into the program.

We have managers work with the members and Pilot to talk not about the past, but about the future. Because there's not much we can do about the past, which typically, as much as employees say they want feedback, they often want recognition and affirmation that they call feedback. Sometimes, it's critical developmental or it's where they stand and it's confirmation of status. So with the future focus feedback, it actually can be very energizing and exciting about what's possible about potential.

Most employees, even senior people, senior executives feel like they have a feedback deficit. All the engagement surveys say this, all the research. And yet employees don't ask for feedback. They don't know how to get that. They don't have to engage in that or even how to consume that.

But, you know, it's one of those things. I had a dear friend of mine that I grew up with. He was from Taiwan and he immigrated in grade school. He sat next to me, and we became good pals, and I showed him banana splits, putt-putt golf, and basketball, and all these things. He went off to an elite university, and we met up in New York about a decade ago. And he said, you know, I'm at an investment bank, a great name bank, and I'm one level from managing director.

He said, all of the folks at that level, the managing director level, want me to be a managing director, but they say that I need to invest in their relationships with them. I need to sort of go golfing with them and eat with their spouses and meet my spouse. I'm just so uncomfortable – in Taiwanese culture, your elders, you feared, you respected, but you never fraternized and spent time. And all these folks at this level, most of them are 10 or 20 years older.

So, his development from his cultural experience was to realize that he was knocking the crap out of his numbers, his deal origination, you know, in his trades and his return on capital, all these great metrics. However, they needed to see that he could partner and hang with them for that.

He's now a managing director, but he didn't know that in his family. And his family, his mom was a professor, and his dad was a government official, and he's from a fairly well-to-do family, but the cultural and racial lens on that, and geographic, changed things so much.

So those are the some of the things that can kind of get in the way, and we often talk about it at Pilot, is the unwritten rules of work, how people really get ahead, which, in that environment, wasn't just your financial metrics.

In banking, even though you think of financial services firm, it would be just money, or metrics. It's not. And so part of what we do in Pilot, we also bring executives into these cohorts. And we have these vulnerable fireside chats to talk about their childhood, the home that they grew up in, the mistakes they've made in their career, the things they wish they learned earlier, the things that people do to screw up, and also who really gets ahead.

And it sort of decodes and creates a more level and transparent playing field because these unwritten rules of work are truly unwritten. They're not in the intranet, they're not in the onboarding training, they're not in the learning management system. And they have to be brought out.

It helps create, you know, markets are more efficient when there's better information, and internal talent markets are markets. And when people from different backgrounds or people that don't work in the headquarters or people that are out from outside the industry or people that work, maybe in a non-revenue generating or client-facing role, learn some of these things, we often see, you know, promotion rates, performance rates, retention, engagement, all these things improve.

It's just democratizing the information that's in the executive's head, they know it, it's inside the organization, but it's just inefficient because it hasn't been shared, so we also are trying to create more efficient talent markets as well.

[00:25:53] Jason Rudman: You mentioned a couple of things there. So, I want to explore the DE&I lens in a post-pandemic world, and what you’ve learned, where are the commonalities to your point and then where are the differences in terms of the members that are part of Pilot and what it has taught you as an organization as to if there are different needs from a DE&I lens.

Are there subtle or maybe not-so-subtle differences in terms of talent development that have been unearthed with the work that you've done? And then let's go a little deeper on the layering effect because I get the executive chats to a point and then we would then also confront the C-suite that continues to look largely like it's looked for the last 40-50 years.

And so how do you marry the executive fireside chat and here's what you need to look for. Here's who succeeds and yet when you look up and you see who's succeeding, It looks kind of homogeneous.

[00:26:51] Ben Brooks: Well, I think on the latter point, I'll address first, just, I think there actually has been a decent amount of progress at the very top levels, Board and C-suite, there's a lot of visibility and there's a lot of demographic diversity at lower levels.

Where we're often missing it is from the 30th to the 90th percentile which are really important jobs, you know, often high-performing individual contributors, managers, management, senior managers, and executives.

That's where we have a huge demographic gaps, right, from diversity. And we still certainly have it in C-suite. You look at an edge of fortune 500 CEOs that are X, Y, or Z demographic and it's not great numbers. CEO is a tough metric. There's such a small ‘n’ on it but there's definitely been some progress.

So, a big part of what we're focused on from an internal cultivation is, we worked with a large health sciences/life sciences company and their Asian colleagues map as disproportionate representation in their organization but some of the least likely to become promoted to management.

And so part of what they wanted to do is cultivate these internal pipelines because, if you look in aggregate, you say, “Oh, we've got 40 percent women, or we've got, you know, 35 percent person of color, we got 10 percent…” and it looks great, but when you stratify it based upon level or compensation or these other things, not so great.

And so where Pilot really focuses – you know, there's a number of folks out there focusing on that Board diversity and there's different metrics or different banks won't invest in companies that don't have at least a female board or a person of color, which I think is fantastic. Right? And you got, you know, state, controllers that invest pension funds. There's a lot of people really pulling those levers.

I think there's far less looking at that middle of the pyramid, emerging leader area where we're focused. Because those people really have an effect on other people from underrepresented and marginalized demographics, because they're their supervisors. At the end of the day, when someone says, how was work today? It's less a function of the COO who sits in a different city who you don't meet with, often a large organization. It's more a function of the supervisor and the team dynamic and the site that you work with. And so that's really kind of who we're trying to reach.

And it's your point about different developmental needs. We've largely found in the research there aren't, they aren't that different. The difference is a couple things –

- How they (developmental needs) get met; if you're a White man versus a Black female advocating for yourself, it comes off differently, it gets navigated. It's a very different dance, right?

So, both people from those different demographics both need to advocate. That's important. And the research says there's no reason why a Black woman shouldn't need to advocate. In fact, a Black woman may need to advocate even more, unfortunately, because the default system is optimized around the majority demographic. So that's one is how those needs to advocate, to prioritize one's development, to get met, look different based on one's demographic.

- And then two, different people want different things.

And sometimes where I think some talent programs go astray is like, here's the women's program, or here's the Latinx, or Latino program, and it assumes that all Black people, or all women, or all LGBTQ people want the same thing, or need the same thing. And those are all pretty diverse demographics within themselves.

So our view at Pilot is we have to tap into the individual, not the demographic because two Black women don't necessarily want the same thing. They don't have the same life. One has kids, one doesn't. Massive difference. You know, one is first gen, one is third gen, you know, like massive differences. And so, we try not to come in with too much assumption or bias because the world's leading expert on each of us, of our lives, our values, our preferences, our needs, our interests, our goals, our desires is ourselves. And so we really try to tap into that rather than tell.

And you can think about someone just like Alvin, you mentioned earlier. Alvin is, you know, a person of color and LGBTQ, right? So, if we have this intersectional part as well, Oh, is this, Alvin needs this for his career because he's LGBTQ? Or he needs this because he's Black? And do those things come together?

Well, Alvin is actually going to know that because based upon the context in geography or the industry which one of those sticks out more, is more of an issue, or feels like more of an identity to him. There's no way I could, from some centralized program, ever figure that out. What I have to do is create the space, to create the support, to create the safety, and to create sort of the stimulus or catalyst for Alvin, or whomever it is, to be one of our members, to figure that out for themselves. I don't know better, and even people from their own demographic don't know better. Then they know for themselves and that's really the empowerment from the inside out.

[00:31:27] Jason Rudman: So, we talked about democratizing talent, democratizing in a very very specific way, so three things in response.

That middle layer, the 30 to 90%, I love it. That's where the impact is. We talked earlier, the higher up you go, the further you get away from the impact. So not only am I seeing somebody that has a lived experience that is similar to mine, but I'm seeing them in a role where they're actually having impact. That's point number one.

Point number two, not only is the experience different, but the learning I think is also different. I know enough in our conversations about Pilot to know that the individualized plan is what makes the difference because it also works with your style. There's a smorgasbord of content and context that marries what it is you're trying to achieve with the way that you learn.

You may respond very very well in a group setting. You may need more one-on-one feedback. So, I think that's also a critical point that is missed in corporate-like development programs that are very much one note. We've got eight competencies. We're going to marry against the eight competencies. And frankly, based on what I saw you do over the last three (3) months, I need you to do this differently or keep doing a little bit more of that.

I'm smiling as well because it's Tuesday and we have two kids, as you know, ten (10) and seven. So, we just came from the teacher conferences and what we didn't get is the same plan for our eldest as we did for our youngest. It was an individualized conversation that highlighted things that are really great. And not surprisingly, two kids, very very different, show up with very different strengths and similar strengths and then some things that are opportunistic. I'll go there and we got some feed-forward in terms of how we can help them.

Key point being that I didn't walk away with Alvin with a mirror image copied plan for our eldest son and our youngest daughter to further add fuel to the individualized nature of what Pilot is delivering.

[00:33:37] Ben Brooks: And I think the difference, right, is that you have a responsibility for your children as dependents, right?

They are not adults. So you have a true paternalistic context in that. Whereas when you're in the workplace, Daddy and Daddy aren't there. Right? So that's what's different, right, is the individual, what the role that you and Alvin are taking, receiving the feedback, having the conversation, talking to your kids, you know, people may have that in a university environment with advisors and resident assistants, teaching all these things.

Then we pop into a workplace, right, and maybe people didn't go to university, but let's assume that that was their track record. You know, you pop into a workplace and that doesn't exist and people kind of expect the manager to be mommy or dad.

And sometimes we treat the employees as if it's a child, right? And so I think that that is also part of it as well, is overcoming this thing that's incredibly functional when we're kids and dependents, which is parental structure and oversight. But then at a time to launch into independent adults, we have to have people realize that they have to be that for themselves.

That's, I mean, people say, “Oh, isn't it great not to have a boss?” and I'm like, well, you know, it's kind of nice to have some direction and some feedback every once in a while versus being you know, in a canoe in the ocean, like which is what entrepreneurship can feel like.

So, I think that what you're saying makes a lot of sense. Each person is different. I think HR often tries to then segment and say, well, we've got five types of employees, or these are the three career paths. And I'm like, it's probably multiple orders of magnitude, more complex with more permutations and the implications of a more diverse workforce mean that people are going to want more and different things.

We try to cram diversity into old structures that assume everyone wants to ascend a hierarchy to have more command and control power when people may have very different expectations and that's one of the big disruptions of the last few years of work Is the slice of the pie of our lives that work occupies is getting smaller.

We used to go to work. Remember that bring your full self to work. Well, work existed as a physical place. But for many people, they're working from home a couple days a week, or as the Pilot team, is remote. First, work is where people live. Work comes to us. And it fits around when the school bus is there, or when we need medical care, or when we're practicing our faith and praying. And we're doing whatever the things are that matter to us.

And so, that's a big paradigm shift, where we have to figure these things out. And there just aren't a lot of structures and our friends have a disincentive to challenge us or to give us feedback. It's like, you don't call me on my crap, I won't call you on yours, right?

And so this is where we really need to create the space and the structure for people to focus on themselves. Whether it's through Pilot or there's many other ways to do this, right? We are one of many, many, many, many, many different ways to do this. We just are excited to get it to people who often never have had anything. It's sort of like soil that's never been touched. And that's why our results are often so quick and so measurable because these aren't the frequent flyers of talent management that get a 360 every year and have had nine coaches.

It's like they've never done these things. They've never been asked the question – do you know your boss's career goals and how are you helping them? Do you lead your one-on-ones or does your boss?

Things that, just a question alone, blow people's minds.

[00:37:01] Jason Rudman: I've practiced the Another child story and so Roman, our son, fourth grade, he led his Spring Conference. He's nine and so the school set it up that he was going to tell us about the areas he was working on.

“Here's the things that are going well, Daddy; here are the three areas, including I have an incredibly messy desk, that I'm trying to get better at.” He's making some progress. We're getting there.

The reason I bring that up is because you can practice it with a nine-year-old. And to your point, I remember taking a very, very different track with a team where I was very much would lead the 1:1.

We come in, I’ve got my agenda or the five things I want to talk about and I pivoted very deliberately (it's actually before you and I connected) and it's a really great practice to say “Tell me what you want to talk about” because what that then opens up is a conversation around prioritization and what's on your mind.

And then I think the challenge as the leader was the variability in the response. You'd either get a Tolstoy novel of here are the, you know, we've got 45 minutes to talk, to check in and you've got 45 things that you want to talk about. Or it was the paralysis of well I think I know what we want to talk about. Or are you going to grade what I put on the paper?

So, there's all of those things that come into play when you start changing the paradigm. And again, I think the changing nature of work is exposing all of these changing paradigms that we have to think through.

You mentioned some results that I was intrigued – intent to stay was the one that I was really, really excited about because we often talk in a business revenue setting perspective of saying that it's much less costly to retain an existing customer and drive loyalty than it is to go get a new one.

And there, within a talent development and a talent recruitment strategy, it has to be much more beneficial to the company and the employee if you can retain the employee, then consistently having to go through churn. Would you just touch on the results that you've seen? Again, the intent to stay, which I know is a marker, but there are others, that showcase the approach that you're employing with your members is actually working.

[00:39:25] Ben Brooks: Yeah. I think it's really important. I talked to an executive at Nestle today, one of our customers. He just talks about the ROI of the program. So I probed, I said, well, tell me more about that. And he said we'll spend millions of dollars on all sorts of things. And your program is one of the few that we can actually point to numbers. And so we look at a few things.

First of all, did the employee actually grow, right? Did they get better at self-advocating, soliciting feedback, managing up, and all these things? And we ask both the employee before and after, but also, we ask the manager to observe, and we triangulate the data.

Typically, the managers observe more growth than the employees. Again, it's hard to read the label when you're inside the jar. So that's part of the reason we triangulate. So, did they grow?

We also measure, did they have an outcome, right? Did they have, did they advocate, did they get a stretch assignment? Did they take on a project? Did they get a different flexible schedule so they could take their aunt to dialysis, so they didn't feel like they had to quit their job?

Those are part of the real-world outcomes. But also, you know, employee retention is a bit of a mind game. What I mean by that is it's a mindset. Do they feel that the opportunities for them at this organization are really good, right?

McKinsey's research said that when people feel they're at a dead end, that's when people leave, especially high performers. And to your point, look, if Netflix, you know has churn and they're, “Oh, we have lose a bunch of subscribers, right?” Their stock goes down, right? Because part of the model is it's expensive to get a customer.

Well, it's expensive to get an employee. You think it's just recruiter costs, forget it.

A new employee in a knowledge worker environment, typically it's, you know, 100-to-200 percent of their annual salary to replace. You got obviously recruiting costs. It takes six months on average to get people to a “meets expectation.” You have the learning curve or the ramp up. You have the burnout of the manager and the team that has to cover while you're recruiting and have an unfilled role. You have quality and productivity and revenue gaps when you have roles unfilled.

It becomes really expensive and so, oftentimes, the reason that people are wanting to leave…

You know, my friend used to be the head of the HR at the National Basketball Association. One day I was in his office, he said, five people, all people of color, all high performers, all had quit that week.

And he was devastated because he called each one right away and said, What's up? Why'd you quit? All five of them had a real clear reason. And zero of them had ever spoken about it. They went off and got a new job.

All five of the reasons were super-solvable, but it was too late. They didn't know how to advocate for themselves. They weren't close with their manager. And this is all very sort of preventable. You know, in HR, they call it regrettable attrition.

So, the intent to stay is where you started this, you know, do you see yourself working at this company in two years’ time? That number goes up when people go through Pilot, often significantly. Our customers also in their own HR systems will measure – do performance ratings go up? Do promotion rates go up?

We had someone at MetLife who is in their national segment of sales, the number one sales producer, and out of Pilot, he increased his sales 30% and worked two hours less a day. He said the best thing he got out of the program was being more in love with his wife, not his sales quota revenue, because he actually was having dinner with her, because he got his stuff together and managed his time better, and his numbers went up, so his boss is happy, his wife is happy, he's happy. It doesn't have to be these either-or, win-lose paradigms. But it requires an inventive nature and a real sense of ownership and self-direction to make those things happen.

But I'll also say, you know, just like the MetLife person, we had a woman at Viacom, you know, she talked to her boss and, to your point around the 1:1s, where the employee's trying to please you, and they're you know, they're, what's the test and did I pass it?

She had always been traveling, but she had a family that was really putting a lot of strain on her. And she thought her boss was someone who wanted her in the field all the time traveling. And through Pilot, she finally shared with her boss that it was a struggle. Her boss didn't even know she had a family!!!

That's how much she suppressed, right? And this is a six-figure earning, you know, manager person. And he said, “are you kidding? Family is the most important thing to me. I can't believe you didn't tell me.”

He was upset but pleased at the same time. And they completely changed how she managed her territory so she could be home a lot more. Because he just didn't know -the iceberg principle – he didn't know what was going on with her. And so by her not even having a solution but just speaking up and sharing more of who she is, she was able to have much better work-life integration and balance and actually formed a closer emotional relationship and alignment with her boss.

So as much as the quantitative results are really important for us in our business model, the impact is also expressed in the qualitative, you know, experiences where we have people that, you know, level set the balance in their marriage of duties at home and have coffee and calendars routines four years later from doing the program.

I hear on LinkedIn from folks, they're doing these things that they learned in our program, that affect their marriages. So that's the part of impact that also can make a difference. And that's what's exciting when executives in HR invest in these things. It's different than just trying to make someone a better employee, a more efficient robot for the machine. You're really trying to make people more effective, which of course benefits the organization. The organization is going to get, you know, financial and operational results. There's also, you're, you're helping make someone a better person to fulfill their untapped potential and isn't that a beautiful purpose.

[00:44:44] Jason Rudman: It is. The word that immediately springs to mind there is empathy. The quantitative is great. Just listening to the anecdote of the leader that didn't know that the person working for them had a family, I come back to the necessary empathetic leadership that is very often, it doesn't show up in organizations because we are the professional robot in the professional setting and we don't feel we can share or we're not given an opportunity to reveal the personal side of us.

It's true, that's like the third rail, so I can't help but think through another conversation that I'm going to have about the power of empathetic leadership, particularly in a remote and a hybrid setting, where you're not face-to-face, and so many of the cues you're not seeing when you're sitting next to somebody and you're staring into a video screen or might even be on a phone call with no video input. And how do we manage through that in order to, per the byline of Pilot, help members “feel powerful at work.”

It's just such a great outcome that we can achieve.

[00:45:57] Ben Brooks: And how do we have employees meet managers and leaders halfway, right? How do you have them share because, you know, there's only, we put too much on managers and leaders in my opinion? We need to have people meet each other halfway.

[00:46:09] Jason Rudman: I was going to go there next. So talk a little bit about that because I think that's incredibly important. While you're democratizing talent development and increasing agency and advocacy amongst your members, I do think as a leader, I'll get that…

This is not a woe is me, because I do think that there are certain things that you have to accept, I think leadership is a privilege, and yet I have found that increasingly the weight of leadership and what we expect leaders to do can be very often overwhelming. And so you just said, you know, I think we expect leaders to do many things and sometimes it's too much.

How is Pilot changing that dynamic with the members that you're serving and the leaders that are part of the program?

[00:46:57] Ben Brooks: Well part of I think, I'm not sure if I would agree that leadership is a privilege. I think our view on leadership is that anyone can be a leader from any seat. That we tried to disaggregate the idea of an executive management role or a people supervision role from the idea of being a leader because we've all seen people in senior executive positions that we would say, for damn sure, are not leaders.

[00:47:22] Jason Rudman: Fair point. Thank you for cleaning that up. That's fair. That's fair. I agree with you having been on the receiving end of it. Yes, totally agree.

[00:47:30] Ben Brooks: Part of what we want to do is whether someone, you know, is a chief revenue officer or a receptionist, we want them to think and act like a leader from every seat.

And so, part of it is having empathy. You know, what's your boss going through? You know, employees will, you know, complain that they don't have a 1:1. We say, well, did you set it up? You think that your boss needs another thing to do to manage? You know, did you put it on their calendar? Oh, your boss just comes in and just, you know, uses a therapy session to dump? Did you set an agenda? Did you tell him or her or them what you wanted to get out of the 1:1?

So, it's this sense of responsibility that, you know, for 40 years, management consulting firms have said, oh, middle management is the thing, and if you were to ask, you know, Fortune 500, you know, heads of HR, do they have good managers or middle managers? I talk to all of them. They say no.

And so we put all money and effort into the managers being better. But managers typically are only 15 to 20 percent headcount in an organization. So four out of every five people in an organization are not a manager. And so that's where I would take exception if we were to say, well, then they're not leaders.

We have 80 percent of people like, not you, right? Or only a select percentage are executives. Well, 95 percent of you not leader. It can be, and so part of leading is leading a relationship. Leading the feedback conversation, leading, you know, whatever it may be. And that sense of ownership, typically when people do that, managers reward that.

And typically, employees are sort of sometimes having the sequence wrong. They say, “What are you going to do for me? And then I'll do something for you,” when in reality, the manager already did something for that person, which is put them in their budget and their FTE count and picked them and hired them. So you take care of the manager and they'll take care of you.

That's the psychological contract we try to unlock and reframe that. And that's what has people's careers really accelerate when they learn that. We actually had someone at MetLife, one of our banner customers. She had multiple people in the program, and she was the person to sponsor it. She actually had some of her own people in it.

She said, you know, Ben, I had a phone call, a couple people in Pilot today, and all three of them in different ways asked, “How can I help you?”

And after the third phone call, I hung up and I cried because I don't know if I've ever had my employees ever asked as good as they are. How can I help me? And I will promise you the ones that do that are going to see bigger bonuses, more opportunity because if they're helping me, I'm helping them.

And it's just rational incentives, right, and it's, and it's respect, and it's all these things, but we don't think about that always in that way, and so that's where people often, you think it just makes very good sense, and you hear a very simple argument, but people are, like, just sort of just, oh, my manager does this, or not that, or she does this.

And come on, like, what is your part? Because your manager is also a human, and they also have sort of their own day job, individual thing, and they actually have their own manager too, and their own everything, and so I think we, to your point, stack too much expectation or responsibility on the supervisor at whatever level they may be in the hierarchy.

And with the unlock at Pilot is to say, no matter whether you're a supervisor in Pilot as an a member or an individual contributor, that there's more you can do. There's more opportunity in what the supervisee can do than the supervisor, also just as a function of spans and layers and control. And so that's really what we're trying to unlock because mathematically that's where the power is. And it's also sort of a clever hack because it's fairly, it's an itch that's infrequently scratched.

[00:51:07] Jason Rudman: Well, I feel that unlock is also connected to the impact quotient. That's a way for somebody to really unlock impact, feel great about what they do within what they call work because they're actually very tied to the priorities of their leader, their supervisor, whatever we want to call it.

So again, it feels like a self-fulfilling circle to your point. And if we could just do more of that, I think that we as individuals within a work context would feel much better about the impact that we were having, because it would be much more explicitly recognized and related to by the people that we work with.

[00:51:48] Ben Brooks: And in tennis, right? It's a volley. You go back and forth and there's velocity to it and there's a reciprocity. But someone has to initiate. We kind of assume the manager is the ball machine that always is cranking the ball and that can't… you're going to wear that person out. You have to have empathy, like you said, for the manager. They likely have a harder job than you. So I think that that's, you know, the humility and the empathy from all parties.

And to realize – one of our coaching series at Pilot is called ‘Including Yourself at Work’ because sometimes, we sit around with a scowl on our face and our arms crossed and like, why am I not included? It's like, well, part of it is like, sometimes you have to include yourself, right? Because like, who is this inclusion committee do you think is selecting you or not? It just doesn't, everyone's busy with their own stuff.

So, YOU have to say, I have a family, right? Or you have to say, I have a thing at 4 o'clock. And whether people know it's your aunt that needs dialysis or not doesn't matter or whatever your thing is, but that's a part of including yourself, your preferences.

You know, you're, you're an outward processor, Jason. I know that. I am too. We talk to think; it works as we talk it out. Other people are going to say “Rudman, like zip it. Give me a second…”

[00:52:59] Jason Rudman:  They have, they do!

[00:53:02] Ben Brooks: Or let me read this overnight rather than an instant reaction. Send me a preview.

So part of it is also navigating the diversity of our preferences and our learning styles. Introverts and extroverts alone. Auditory and visual learners alone…is a huge difference. In communication channels. Times of day, what are our peak and off-peak hours, the morning, you know, early birds versus the afternoon or night owls.

Those are all really important things we also have to navigate and have empathy towards because it can actually make a huge difference.

If you find that your boss is always grumpy in your 1:1s and you kind of do a little inquiry as to why, and it's because they're not a morning person, or it's after the worst meeting of their week, try doing a 1:1 at a different time. Put on your lab coat. Do an experiment, right? Take responsibility, get the context.

That's the thing that you can never do from the headquarters of a $10 billion company, to figure out that level of nuance and permutation. It has to be done in the relationships and at the individual level.

[00:54:08] Jason Rudman: There is so much for anybody listening to this conversation to unpack. You've dropped so many nuggets of wisdom. You're nine years in. Again, I'm going to look it up, I could have been rude and looked it up here, but we're on video, so I'm not going to do that, but I will figure out what nine equates to. How would you summarize the impact that you believe you've had in nine years with Pilot?

[00:54:34] Ben Brooks: I guess it might be contextual to whom. You know, surprisingly the first thing I thought about was to me. Maybe that's self-centered, but I, but just...

[00:54:43] Jason Rudman: No, well, you know because I think the personal and the professional are so inextricably woven because my follow-up question was going to be, how have you reflected on the journey of Pilot to the personal, in terms of what you were looking to achieve. So, what would you evaluate as the impact to you then as a person, having spent nine years taking a risk, going out on faith, being uber-resilient in periods of uncertainty?

How would you reflect on what it has taught you, changed you, evolved you as a person?

[00:55:19] Ben Brooks: Well, you know, I will say that it'd be very easy to look at just the positive side of the ledger, right? Of everything that's great about it. And I think that's the sort of, again, the information asymmetry we see in the fetishization of, you know, innovators and entrepreneurs, et cetera.

But, you know, it's had an incredible toll on me, you know. Friendship and social life is declining, but relationships get screwed up. I've had health, I've had personal debts, I've had, you know, anxiety and mental health chams, all sorts of things.

So it's come with a great price, but I think on the positive side of the ledger, my ability to navigate and solve problems and figure things out and have perspective and maturity, things that would spin me out for days, don't even make me flinch today.

And, you know, my, my sophistication in running a business and managing people and kind of navigating the potholes and the speed bumps and in the, you know, washboard on the road along the way has grown. But really, I think just the satisfaction that knowing that I make a difference and that I've, you know, found a calling for myself.

Any day, our ticket could be called. Today could be my last day or your last day. And if it was, I would be really proud of what we've done and the impact I've had and know that, you know, we're excited to build and we have a multi-year strategy and we're going to massively scale up our impact. But, even what we've done to this day, without doing anything else, has been deeply meaningful, which makes me really proud and really satisfied back to that other S word.

[00:56:51] Jason Rudman: Well, there's always a ledger. It can't always be, you know, the credits and the debits work together. And what I take away from what you just said, and I want to give it back to you, is you are changing people's lives for the better

If you think about the More Elephant tagline of listen, learn, live, better, then members of Pilot are living a better, fuller, more powerful life, I would argue. The numbers are great, but so are the qualitative impacts that you're having. The anecdote of the husband that now has more time. Time is such a valuable commodity. To actually make a marriage better. That's huge. And that might not have been, Ben, what you thought you might have been solving for when you when you started Pilot.

[00:57:39] Ben Brooks: I've never been married. I'm not a marriage expert. I'm, you know, all that. But surprisingly with one-on-one coaching, and with Pilot, marriages tend to improve. And it takes one, right? We have a thing that takes two, it takes one. And, one person can transform a relationship, including with themselves. And so I think that that's, you know, that's the satisfying thing.

Because we got one shot at life, we got one life to live. It's often shorter and we get less done than we think. And so making that matter, and really affecting at the end of the day that answer at the dinner table, or over FaceTime, or on text. How was work today?

If I can affect that for folks without changing their jobs, without any of that, cause that's usually the answer is - get him a different boyfriend, right? Get him a different job.

I'm not doing that. I'm affecting right where you are. If the grass is brown, water your own grass, and changing that answer, that is deeply meaningful.

[00:58:36] Jason Rudman: I love it, and maybe I'm a little biased because I've spent five years working with you personally. However, completely subscribed to a path to making the grass greener.

[00:58:49] Ben Brooks: Yes.

[00:58:49] Jason Rudman: On my terms. That's all another conversation, Ben. That we probably may….

[00:58:53] Ben Brooks: I see a follow on episode. I mean, you got a lot of guests.

[00:58:56] Jason Rudman: A follow-on episode! Let me end with a shout-out from you which is, how do people learn more about Pilot and Ben Brooks?

[00:59:06] Ben Brooks: So Pilot, our website is www. pilot. coach. C O A C H; www. Pilot. coach.

We're on LinkedIn and a bunch of other platforms that way. I would love to connect with anyone listening. I have a big LinkedIn network and I share a lot of stories and resources and things. Find me on LinkedIn. I'm Ben Brooks, NY in New York, Ben Brooks NY on Twitter, Instagram, LinkedIn, all those different platforms. I'd love to connect with people around the world and be of service and hopefully have more impact as I grow my community and I grow my network.

And I am definitely excited, Jason, for More Elephant with you.

[00:59:44] Jason Rudman: Well, I appreciate it. I appreciate everything that you have done as a coach, as a friend. Sometimes the prods have been painful. They've always been meaningful. And you have, over the course of five years, been such a great mirror for me to continue to elevate and appreciate what's inside of me, and to get it out into the world, and to experiment, and continue to curate.

So, I owe you a huge debt of gratitude, and I appreciate, again, everything that you've been able to do personally with me. And from this conversation, I think the impact that you're going to have on our listeners, to just take a moment to say less, listen to this podcast, learn some great wisdom, and some great things that you can do immediately to feel more powerful at work.

So, Ben, I thank you for your time. And talk soon.

[01:00:39] Ben Brooks: Glad to be here.

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